Dear Friends,
I checked "The Death of Ivan Ilyich" out of the Harold Washington Library a few weeks ago and brought it to the park.
I read most of it on a bench, with Oliver, my cat, parked beside me in his stroller. Yes, a stroller. Yes, a cat. He is, by unofficial neighborhood vote, extremely popular, and he tolerates our walks with a patience I have not earned.
A friend of mine, a philosophy professor who knows exactly what I do for a living, is the one who put the book in my hands. She didn't explain why. I found out on my own, a few chapters in, that I was going to fight with it.
That fight has turned into something I didn't plan for. I started a reading practice this year, real books chosen for what they might do to my thinking rather than what I could do with them, and Tolstoy was the first assignment. It's already adding a dimension to this work that wasn't here before: less lived observation and client pattern, more philosophical spine underneath it.
It's a book everyone quotes and almost no one actually reads, which made the choice feel even more pointed once I sat with it. A few chapters in, I understood exactly why she'd picked it for me. Tolstoy wrote it about exactly the territory I work in: a man whose life was built on the wrong foundation, who doesn't find that out until it's nearly over.
Here's the shape of it, if you don't know the story. Ivan Ilyich is a judge. Respectable, correct, careful to want what a man in his position is supposed to want. He climbs. He furnishes a house exactly the way a man of his rank furnishes a house. Then he gets sick, in a slow and undiagnosable way, and over the length of the book he dies. What kills him, in the end, isn't only the illness. It's the realization, arriving in pieces over his final months, that the life he built so carefully might have been the wrong one.
I expected to find that devastating. I did. But I didn't expect to find myself arguing with the book by the time I closed it.
Here's where I land differently than Tolstoy does.
The novella treats Ivan's deathbed clarity as the redemption. In his final hours, something in him lets go. The fear leaves. He sees, finally, what mattered and what didn't, and there's real peace in it. Tolstoy writes it as an arrival, as if getting the insight is the whole of the work.
I don't think it is.
Ivan gets free in that room. I believe that. What he doesn't get, what he never gets, is any capacity to act on what he now understands. He's dying. The clarity shows up at the exact moment it can no longer be spent on anything. That's not redemption. That's a cruelty dressed up as one.
Freedom and agency get treated as the same thing in that final chapter, and they aren't. Freedom is the interior release: the fear loosening its grip, the honest look at what you built and why. Agency is something else entirely, the actual capacity to take that clarity and do something with it. Change the house. Change the marriage. Change the thirty years, if thirty years are still in front of you.
Ivan Ilyich gets the first one. He never comes close to the second.
This is the piece of the story I keep returning to, because it's the piece that matters most for anyone reading this newsletter. Most of you are not on your deathbed. You have the thing Ivan didn't: time left to spend the insight on. And I think that changes the entire assignment.
The real work isn't waiting for the kind of clarity that shows up when everything else has been stripped away. It's going looking for it decades earlier, on purpose, while you still have the agency to act on what you find. Orientation before prescription. You have to know where you actually stand before you can decide where to go, and that has to happen while going somewhere is still possible.
There's a servant in the book, Gerasim, who tends to Ivan in his final months without any of the performance everyone else in the house puts on. He's the only honest person in the story, and he's the only one with nothing to lose by being honest. I keep thinking about how much easier that kind of honesty is for someone who isn't invested in defending the life he's already built.
That's the harder version of this question, and the one I don't have a full answer to yet: can you get Gerasim's honesty about your own life while you're still the one living it? Or does it take dying, even a little, to see it?
I don't know yet. That's the whole point of starting a reading practice instead of writing a conclusion.
Warmly,
Cara
Future Identity Strategist
Founder, Good Morning Freedom
In case you wanted to see Oliver. Here he is at our usual park bench.